Sodium Bicarbonate → 6-Fluoro-3-[1-(8-methoxy-2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-1,2,3,6-tetrahydro-pyridin-4-yl]-1H-indole

HRID 1823840Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1823840
CC1C=CC(S(O[CH2:12][C@@H:13]2[O:18][C:17]3[C:19]([O:23][CH3:24])=[CH:20][CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=O)=O)=CC=1.[F:25][C:26]1[CH:34]=[C:33]2[C:29]([C:30]([C:35]3[CH2:36][CH2:37][NH:38][CH2:39][CH:40]=3)=[CH:31][NH:32]2)=[CH:28][CH:27]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O.O1CCCC1>[F:25][C:26]1[CH:34]=[C:33]2[C:29]([C:30]([C:35]3[CH2:36][CH2:37][N:38]([CH2:12][CH:13]4[O:18][C:17]5[C:19]([O:23][CH3:24])=[CH:20][CH:21]=[CH:22][C:16]=5[O:15][CH2:14]4)[CH2:39][CH:40]=3)=[CH:31][NH:32]2)=[CH:28][CH:27]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 110530726-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 11792133[(2R)-8-Methoxy-2,3-dihydro-benzo[1,4]dioxin-2-yl]methyl 4-methylbenzenesulfonate

Produkt 1

HCID 102719506-Fluoro-3-[1-(8-methoxy-2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-1,2,3,6-tetrahydro-pyridin-4-yl]-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

[(2R)-8-Methoxy-2,3-dihydro-benzo[1,4]dioxin-2-yl]methyl 4-methylbenzenesulfonate (0.30 g, 0.86 mmole), 6-fluoro-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (0.60 g, 2.7 mmole) and sodium bicarbonate (0.80 g) were added to a mixture of dimethylformamide/tetrahydrofuran (1:1 v/v, 20 mL) and the reaction mixture was refluxed under nitrogen for 18 hours. The solvent was evaporated and the residue partitioned between 400 mL each of water and methylene chloride. The layers were separated and the methylene chloride solution was washed with water and saturated aqueous sodium chloride solution, dried over anhydrous potassium carbonate and filtered. The filtrate was evaporated in vacuum and the residue crystallized from chloroform containing 3% methanol, giving 0.23 g (68%) of the (S)-enantiomer of the title compound as an off-white solid, m.p. 184–185° C.

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed under nitrogen for 18 hours
  2. customThe solvent was evaporated
  3. customthe residue partitioned between 400 mL each of water and methylene chloride
  4. customThe layers were separated
  5. washthe methylene chloride solution was washed with water and saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous potassium carbonate
  7. filtrationfiltered
  8. customThe filtrate was evaporated in vacuum
  9. customthe residue crystallized from chloroform containing 3% methanol

Quellen und Nachweise

ORD-Eintrag
ord-8e1ab0290e2040acbec7e6446c5b1141
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07041683B2

Notizen zur Reaktion

Wird geladen…